Abstract: In this paper, we examine the way wildlife figures in the geographical imaginary and how shifting relations with animals reaffirm boundaries between the civilized and wild that sits at the core of the colonial project. Using the production of the boundary between the urban/wild as a starting point, we consider the complex and shifting relationships between urban wildlife and the production of the hegemonic colonial subject in the township of York, which would later become Toronto in 1834. Focussing on the figure of the bear, we explore the colonial project in 19th century as it was shaped through emerging contact zones that reordered urban-wildlife relations. We move through examples of urban place making, beginning in 1809 in downtown York with the legend of Lieut. Fawcett who slashed a bears head open with his sword. We then work through other heroic tales of killing bears for sport and self-defense in the performance of “Candian-ness”. We conclude then conclude with the establishment of the Riverdale Zoo in 1889 an institution that is deeply entangled with the longer histories of torture and confinement of the bear, practices that haunt our recent past.